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Having grown up together, Nathan, Rick and Leo all agreed to enlist in the United States Army during World War II. Their only condition was that they were kept in the same unit, so all three men were sent to Guadalcanal during the war. Unfortunately, during a fight Nathan was struck by a piece shrapnel and Leo tried to take care of him before leaving to go help other wounded soldiers in the field. Nathan and Rick were both killed on November 14, 1942 when a bomb was dropped on the medic tent. Leo died later that same day. However, Leo was rewarded for his bravery by becoming a Whitelighter, while Rick and Nathan became trapped as lingering spirits.

In 2002, Leo's wife Piper Halliwell insisted that Leo went to a veteran reunion as his own grandson. However, Leo still harbored guilt over the death of his friends and didn't want to go. When the spirits Rick and Nathan found out that Leo Wyatt's 'grandson' would be attenting, they sought to take revenge. When they attacked Leo at the manor, they discovered it was Leo himself when he healed from a knife wound. They realized that they couldn't kill Leo himself, so they decided to go after the ones closest to him.

Rick crushing Piper's heart.

Rick and Nathan proceeded to kill one of Leo's charges, Maria, and forced him to watch. Leo's guilt then blocked his powers as the brothers went after his wife. Rick then attacked Piper and crushed her heart by reaching into her. However, as Piper's spirit began to leave her body, she used the spell to vanquish a spirit. Paige reminded Leo of all the lives he saved and he regained his confidence and powers in time to keep Piper from dying.